73108-78-8

Usage

InChI:InChI=1/C16H13NO/c1-11-7-8-15-13(9-11)10-14(16(18)17-15)12-5-3-2-4-6-12/h2-10H,1H3,(H,17,18)

Upstream product

• 122778-78-3 3-(5-Methyl-2-trichloracetylaminophenyl)-2-phenylcyclopropenon 
• 93500-92-6 N-p-tolyl-α,β-dibromohydrocinnamamide 
• 108-90-7 chlorobenzene 
• 71-43-2 benzene 
• 29289-13-2 2-iodo-4-methylaniline 
• 536-74-3 phenylacetylene 
• 13939-06-5 molybdenum hexacarbonyl 
• 6277-67-4 4-nitro-1,3-diphenyl-butan-1-one 
• 539-44-6 N-4-methylphenylhydrazine 
• 144-62-7 oxalic acid 
• 1200688-18-1 C₁₆H₁₃NO 
• 1176043-22-3 C₁₆H₁₁N 
• 98-86-2 acetophenone 
• 13228-36-9 5-methyl-2-phenyl-1H-indole 

Relevant academic research and scientific papers

Supported Palladium Nanoparticles-Catalyzed Synthesis of 3-Substituted 2-Quinolones from 2-Iodoanilines and Alkynes Using Oxalic Acid as C1 Source

3-Aryl/alkyl-2-quinolones were synthesized employing microwave assisted multicomponent reaction of 2-iodoanilines, terminal alkynes and oxalic acid dihydrate ((CO2H)2 ? 2H2O) under polystyrene supported palladium (Pd@PS) nanoparticles-catalyzed conditions. The use of a heterogeneous palladium catalyst was explored first time for 2-quinolone synthesis involving carbonylation reaction employing (CO2H)2 ? 2H2O as a solid and bench stable carbon monoxide (CO) source. The reaction exhibited good substrate generality for 2-iodoanilines and alkynes with wide functional group tolerance and good regio-selectivity. The ligand free operation, recyclability of heterogeneous Pd@PS catalyst and use of bench stable C1 source are the invaluable merits of the protocol. (Figure presented.).

Synthesis of 3-substituted quinolin-2(1H)-ones via the cyclization of o-alkynylisocyanobenzenes

A facile synthesis of various functionalized 3-substituted quinolin-2(1H)-ones through Ag(i) nitrate-catalyzed cyclization of o-alkynylisocyanobenzenes is described. The reaction allows rapid and convenient access to 3-substituted quinolin-2(1H)-one scaffolds in moderate to good yields.

Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones

3-Substituted 2-quinolones are obtained via a novel metal-free transannulation reaction of 2-nitroolefins with 2-substituted indoles in polyphosphoric acid. This acid-mediated cascade transformation operates via the ANRORC (Addition of Nucleophile, Ring Opening, and Ring Closure) mechanism and can be used in combination with the Fisher indole synthesis to offer a practical three-component hetero-annulation approach to 2-quinolones from arylhydrazines, 2-nitroalkenes, and acetophenone. An alternative entry to this chemistry employing the alkylation of electron-rich arenes and hetarenes with 1-(2-indolyl)-2-nitroalkene has also been demonstrated.

Highly efficient modular metal-free synthesis of 3-substituted 2-quinolones

A modular approach to 3-substituted 2-quinolones via a cascade annulation reaction between 4-nitroketones and hydrazines has been developed.

Metal-free transannulation reaction of indoles with nitrostyrenes: A simple practical synthesis of 3-substituted 2-quinolones

3-Substituted 2-quinolones are obtained via a novel, metal-free transannulation reaction of 2-substituted indoles with 2-nitroalkenes in polyphosphoric acid. The reaction can be used in conjunction with the Fisher indole synthesis offering a practical three-component heteroannulation methodology to produce 2-quinolones from arylhydrazines, 2-nitroalkenes and acetophenone.

Microwave-assisted, palladium-catalyzed carbonylative cyclization - Rapid synthesis of 2-quinolones from unprotected 2-iodoanilines and terminal alkynes

Palladium-catalyzed cyclocarbonylations of 2-iodoanilines with various terminal alkynes have been carried out by the use of commercially available molybdenum hexacarbonyl as a convenient and solid carbon monoxide source. The reactions were conducted at 160 °C for 30 min under microwave irradiation and in the presence of Et3N in THF, affording the corresponding 2-quinolone derivatives in good regioselectivities and yields.

Pharmaceutical compositions comprising 2-quinolones

The invention concerns a pharmaceutical composition having an activity on the proliferation of clonogenic cells in tumours and comprising an efficient amount of a compound selected among the compounds of formulae (I) and (Ia) wherein: X, R1, R

Synthesis and Properties of o-Hydroxyphenyl- and o-Acetylaminophenyl-Substituted Cyclopropenones. A Novel Thermal Transformation of Functionalized Cyclopropenones

The ortho-functionalized arylphenylcyclopropenones 3 are prepared via the West method and their spectroscopic and chemical properties are reported.The cyclopropenones 3 undergo thermal transformation to give heterocycles 7, 8, 12, photochemically they are

Synthesis of 3-Arylcoumarins, Thiacoumarins and Carbostyrils

3-Arylcarbostyrils (2a-f), coumarins (2g-j) and thiacoumarin (2k) have been prepared by a generalised method from α,β-dibromohydrocinnamoyl derivatives (1a-k).The intermediate dihydrocoumarins and dihydrocarbostyrils (3, Y = O, NH) have been prepared which on acid treatment furnish 2.However, treatment of 3 with a base affords the 4-arylcoumarins and carbostyrils (4).

A New Route for the Synthesis of Coumarins, Thiacoumarins and Carbostyrils

3-Arylcarbostyrils, coumarins and thiacoumarins (3) have been prepared from the respective β-aryl-α-bromodihydrocinnamoyl derivatives (2) by treatment with AlCl3.The β,β-diarylacrylic acid derivatives (4) and (9), obtained from 2, on reaction with AlCl3 afford 4-arylcarbostyrils (5) 6-methyl-4-phenylthiacoumarin (10) respectively.However the oxygen analogs (11) give 3,3-diphenyl-1-indanone (12)